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Updated March 23, 2023You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.
Onboarding is the process of integrating a new employee into an organization.
Onboarding plays a decisive role in the success of any new hire, and in your overall culture. Given the complexities of remote work, this is even more important in a remote context. The default setting in a co-located office environment is that people will ask those around them for clarification on how things are done, or watch what others do to learn more about the culture. They learn norms and behaviors as well as problem-solving strategies, how to use tools, and the context of their work within the company through proximity to the team they work closest with or their line manager. This can be efficient in a co-located team (although as many people can likely attest, it’s not a guarantee that it will be!).
In a remote team, need-to-know, ad hoc onboarding won’t work. You run the risk of organizational knowledge gaps being filled with guesses, and risk reaching that critical three-month mark and noticing a remote worker still isn’t productive.
Onboarding someone remotely starts the moment the candidate says yes. Good onboarding includes making sure they are set up with the following prior to their first day.
Send through their contract and role description. Typically you’d do this via Docusign or a similar online tool, since they are not there for you to hand them physical copies.
Enable access to all critical tools to do their job.
Enable their company email and calendar access.
Invite them to all relevant events on their calendar.
Let them know what time they’re expected to log in, or have their first team interaction.
Send them a “who’s who” email: detail every member of their team, who can be contacted with questions, how they relate to the new hire’s role, and what your expectation is for that relationship (for example: a peer, a key stakeholder, someone to be kept lightly informed). As a remote or distributed company, it is wise to create a public org chart that can be accessed by employees at any time.
Have a “meet and greet” meeting over video.
Make sure they have what they need for tools and access.
Share their 30-60-90 day plan.
Show them around: point out what tools are used and how, and invite them to relevant interest groups or chat channels. Again, your code of conduct, norms and expectations around tools, as well as where to find relevant information, should be documented in your company handbook—you’re just helping them get a jump-start.
Introduce them to their team. Depending on the size of the team, this may be done in a video conference with everyone, or in a Slack channel. Ideally, the new person has some form of one-on-one video chat with everyone on the team as soon as possible after starting, as this helps establish more direct, personal connections.
The Day One Document is a prime example of our belief in writing everything down. The key to designing a thorough onboarding program that gets new people acquainted quickly is over-documenting everything.Noah Brier, co-founder, Variance*
Here’s an example Day One Schedule from Percolate, a company previously founded by Noah Brier. This level of detail is ideal for remote onboarding.
Source: Percolate (First Round)
Typically, the first 30 days are about learning, the next 30 are about contributing, and the final 30 are about reaching independence (or leading, depending on the role). An effective written plan states concrete goals for each time phase, and ends with the final goals of the position (which essentially will be to independently execute their job description).
As a manager, you will have a corresponding document with your own goals to support the new hire: for example, finding an appropriate project for them to own at the 30-day mark, or delegating a significant responsibility at the 60-day mark. In a remote context, it’s important for both sides to have a clear expectation of the job, and of what success looks like.
HubSpot has excellent templates for 30-60-90 day plans, for both new hires and their managers.
Brené Brown’s work and research in Dare To Lead shows that organizations that have clear expectations also foster higher levels of vulnerability, trust, and connection. The motto “clear is kind” is one of the most important things a manager of remote workers can remember. When Brown mentions “clear,” she speaks of a highly descriptive activity—“painting done”:*
“Painting done means not just assigning a task, but explaining the reason—clarifying how the end product will be used.
Providing color and context—the purpose, not just the mechanics.
Sharing the reason for a task helps uncover stealth expectations and stealth intentions, cultivates commitment and contribution, and facilitates growth and learning.”
Remote workers, like all workers, will fail if they don’t have the clarity and context they need to execute a task and succeed in their role. This is true of all roles, but in a remote setting where context is more easily lost, it’s a particular risk. A short-term investment in thorough onboarding can make a major difference in how productive a new remote worker is as a long-term teammate.
The second major challenge with successfully onboarding a remote team member is integrating them into the culture. Culture gets shared in casual and social interactions, so co-located teams will find it easier to maintain a certain culture (whether that culture is “good” or not is unrelated—in-office and remote teams can both be healthy or toxic). New hires in a remote team will have fewer interactions to observe, and so the signals they’re collecting to understand expected cultural behaviors are more limited. Additionally, in a growing team, new people may band together, viewing the fellow new hire as the safest person to ask a potentially “dumb” question, rather than their teammate or manager. This risks sub-cultures developing as new hires onboard, further fragmenting the culture away from the overall company’s direction.
When people say that “maintaining culture when you hire remotely” is hard, this is what they mean. The default is a forking, branching culture, with each “generation” of new hires developing their own ethos; maintaining one common shared culture takes continued, focused work. David Loftesness, who has worked at Twitter and Eero, suggests a few tactics for dealing with changing culture as people onboard:
Fostering an understanding of what each team does, what their challenges are, the basic act of putting names to faces after a meaningful interaction, is a great way to sidestep factions down the road … Get new hires in a room with your veteran employees, for example, to maintain a thread to your earliest days. Encourage them to share stories, both difficult failures and energizing successes. This can give the new folks some perspective of what the old-timers went through to get the company to where it is today.*
Ensuring that new hires are surrounded by veteran teammates who have an explicit mandate (and the time) to support them helps teams stay culturally cohesive as they grow. Fully remote companies Buffer and GitLab both use a “buddy system” for onboarding and building culture with new hires.
In a buddy system new hires are assigned one or more peers in addition to their line manager. Peers can act as a role buddy, to help them succeed in their role, and/or as a culture buddy, responsible for onboarding the new hire into the company culture.
importantThe job of the role buddy is to help the new hire execute their 90-day plan, not to evaluate or test them. This is important, because new hires need a safe person who they can ask questions, and an evaluative person is by definition not entirely safe. That’s why a line manager alone can’t provide this level of peer support to the new hire.
At Buffer, the role buddy is responsible for showing the new employee the ropes of their role, helping them achieve their tasks, and answering any questions. This person is usually a member of the same team and in a similar role. Ideally, they have several hours a day of timezone overlap as well. The role buddy has less work individually assigned to them and will meet regularly with the new hire’s line manager to understand how to support the new hire.
The culture buddy is another peer, and together with the new hire, follows an explicit course of cultural onboarding, meeting once a week for six weeks. The relationship officially ends after that time, but many buddy pairings remain close. The culture buddy is responsible for helping the new hire acclimate to remote work, find the schedule and set-up that works for them, explain cultural nuances like “rather than phrasing your request like that, we usually say it like this and include this information” or “in this team, that emoji is considered passive-aggressive.” They also share any helpful informal dynamics, such as “product managers here are considered on par with managers—they’re important decision-makers,” or “instead of asking someone when they’re free, we like to look at the person’s calendar and schedule an appropriate time.” These are the non-obvious, yet critical things to help new team members feel at home and be accepted.
Buffer also has explicit meetings, for an hour each week, where the team discusses the company values and any challenges that arise when living those values. New hires are asked to do a written reflection every two weeks and share that document with their culture and role buddies, as well as their manager. This helps everyone be clear and explicit about every aspect of the onboarding, how the new hire is feeling and performing, and how the company can best support them.
A gelled team (or integrated team) operates as a collective unit where the output is more than the sum of each individual contribution. A key indicator of gelled teams is a high level of psychological safety.
In a remote team, the factors that may contribute to a feeling of psychological safety are more rare, like face-to-face engagement and general social activity. Leaders need to work intentionally to help teams gel. Thinking of teams as being entities that go through development stages makes it easier to anticipate challenges and overcome them.